Assessing teams that might have use for Jacoby Ellsbury or Chase Headley

Last week, E.J. touched upon the Yankees’ offseason budget and how a few salary shedding trades could be in the club’s plans. E.J. also wrote about Masahiro Tanaka’s decision to remain in the Bronx and how it has increased the likelihood of the Yankees seeking to move salary off the books. Fortunately — Unfortunately? — the Yankees have a couple of hefty payroll holds on the books next season that are obvious candidates for salary dumps: Jacoby Ellsbury and Chase Headley. The duo will make up about $35 million in 2018, or 17.8% of the $197 million luxury tax threshold that Hal Steinbrenner would like to stay under.

Just because it makes sense to eschew both of these players, at least from a financial perspective, doesn’t mean it’ll be easy to find takers. The other 29 teams aren’t lining up to take on a 34 year-old center fielder owed $68 million through 2020 who hasn’t produced a season of more than 1.1 WARP since 2014. 2014! Yeah, it’s going to be hard to move Ellsbury without the Yankees taking on a significant portion of the salary. One other obstacle is Ellsbury’s full no-trade clause, but perhaps he’d be willing to leave New York for more playing time. On the contrary, Headley is the far more affordable of the two trade candidates, though asking another team to fully absorb all $13 million of his 2018 dues is likely to be returned with a chortle. That said, the switch-hitting third baseman does have a couple of redeeming qualities that make him more attractive to potential suitors: his contract will be complete after 2018 and he’s still a capable performer (2.3 WARP last year). Ultimately, in order to find a taker for either of these two, the Yankees will need to find a match that needs either a center fielder (or left fielder?) or corner infielder and has the wherewithal to add payroll. Or, someone looking to do the team a big favor.

There are plenty of teams that will sign or trade for outfielders and corner infielders this winter, but that doesn’t mean all of them would want to add Ellsbury or Headley. For example, teams likely not to contend next season, such as the White Sox or Athletics, who didn’t get much production from center field last year, wouldn’t waste their time considering Ellsbury. Basically, a club willing to inquire is likely trying to contend in 2018. Otherwise, there’s not much of a reason to take on such a financial commitment.

In cycling through the other 29 big league clubs, finding a potential match for Ellsbury is almost impossible. Only a couple come to mind, and even the following two take a bit of a stretch to make sense with: the Giants and Mariners. The two teams won 64 and 78 games this season, respectively, though it stands to reason that both clubs would like to contend next year considering the current makeup of its rosters. Both teams still have excellent core players (Buster Posey and Madison Bumgarner for the Giants; Robinson Cano, Nelson Cruz, and James Paxton for the Mariners) though those players’ peaks are likely nearing an end (Paxton the lone exception). Both clubs could use help in the outfield: Seattle’s starter in center field, Jarrod Dyson, is a free agent and San Francisco got little production from left and center field (though Denard Span is still in tow). A more sensible path to filling either of the team’s outfield needs could be to sign either Lorenzo Cain or J.D. Martinez, though only the former can play center field. Should the Mariners and Giants lose out on the big splash, perhaps taking on, say, $15 to $20 million of Ellsbury’s remaining $68 million salary is reasonable. Hey, one can hope!

When it comes to Headley, finding a prospective buyer isn’t as unimaginable as it is for Ellsbury. Two teams come to mind: the Angels and Giants (yes, again). Both teams didn’t get much out of the hot corner this year, so Headley would represent a certain on-field upgrade. For the Halos, the combination of Yunel Escobar and Luis Valbuena struggled in 2017, failing to reach a measly 1 WARP at the hot corner. For the Giants, Eduardo Nunez was the guy at the position until he was traded away. Otherwise, the amalgamation Ryder Jones, Pablo Sandoval, Jae-Gyun Hwang, Conor Gillaspie, Christian Arroyo, and Aaron Hill didn’t cut it. That’s a lot of flops, though Jones and Arroyo have some prospect sheen at least. We already went through the Giants potential to contend next year, so let’s quickly touch on the Angels: they have Mike Trout. Also, they won 80 games without him for much of last season, so it’s pretty easy to see them being in contention next year with a healthy Trout. One more plus on the Angels side: it can’t hurt that its general manager, Billy Eppler, used to work in the Yankees’ front office. From a financial perspective, perhaps the Yankees could shed more than half of what Headley is owed next season, considering that it’s only a one year commitment and he’s a solid player.

Trade partners aside, is it sensible for the Yankees to deal one or both of these two from an on-field perspective? It’s not much of a question for Ellsbury, as he’s already crowded out by Aaron Judge, Aaron Hicks, Brett Gardner, and Clint Frazier in terms of ability. The practicality of moving Headley, on the other hand, isn’t as clear. Moving him would create a void at third base, as Todd Frazier is a free agent and Miguel Andujar is unlikely to be handed the job. In fact, it’s probably more expensive to eat some of Headley’s salary and subsequently re-sign Frazier rather stand pat. Plus, Headley’s one remaining year on his deal makes him a good option as a holdover until Manny Machado’s free agency after 2018.

If you’ve made it this far, you might be wondering why I didn’t consider moving Gardner to shed salary. It’s become a yearly routine to discuss him as a trade candidate during the hot stove season, and this winter will probably be no different. He’s in the final year of his contract and costs $13 million next year toward the luxury tax cap. Plenty of clubs would be happy to add Gardner, though the Yankees are certain to exhaust all options with moving Ellsbury before moving on to its stalwart in left field.

It’s a fool’s errand to speculate about baseball trades, especially ones with large financial ramifications. Yet, here I am trying to find a landing spot for Jacoby Ellsbury and Chase Headley. It’s not ridiculous to ponder potential suitors for Headley, but it’s somewhat humorous to suppose that some team would be interested in acquiring Ellsbury. Brian Cashman gets a lot of credit for his trade history because it seems like the Yankees always come out on top, but finding a trade partner for a sunken cost like Ellsbury while obtaining some salary relief would have a chance to be his best work yet.